Outside Sales Representative and Trainer

Outside Sales Representative & Trainer

About Us

At Cleft of the Rock, we believe in serving people first. We help businesses and individuals protect what matters most through supplemental insurance solutions — but our real mission is to care for others and provide peace of mind. Our culture is built on compassion, connection, and purpose.

Your Role

As an Outside Sales Representative & Trainer, you'll do more than sell — you'll serve. You'll connect with local business owners, listen to their needs, and help them find insurance solutions that make a real difference. Along the way, you'll also train and mentor others, using your natural warmth and people skills to help your team grow and succeed.

Key Responsibilities:

Build meaningful relationships with business owners, managers, and employees

Present supplemental insurance solutions that align with client needs

Conduct group presentations and one-on-one consultations

Train and support new team members, helping them build confidence and success

Follow up with clients regularly to ensure satisfaction and continued support

Work closely with your manager to set goals and grow your impact in the field

What We Offer

Comprehensive training and mentorship to help you thrive

Weekly draw pay plus commissions and bonuses

Incentive programs including cash rewards, recognition, and travel opportunities

Opportunities for professional growth and leadership development

A supportive, mission-driven team environment centered on people and purpose

 

Who You Are

Compassionate, service-minded, and genuinely care about helping others

Skilled at building trust and creating lasting relationships

Encouraging and supportive — a natural mentor and team player

Positive, motivated, and driven by making a meaningful impact

Licensed in Health & Life or willing to obtain a license (licensing assistance and reimbursement provided)

Company: Cleft of the Rock

Compensation: $85,000 - $105,000 per year with draw pay, commissions, and bonuses

Schedule: Monday–Friday, weekends as needed

Location: In-person, business-to-business and individual sales

Join Us

If you're looking for a career where you can build relationships, serve others, and make a lasting impact, Cleft of the Rock offers the environment, training, and purpose to help you succeed as an Outside Sales Representative & Trainer.